Cardinals Should Not Pursue Dustin May Reunion This Offseason

St. Louis made a smart move signing Dustin May last year, but they should avoid pursuing him again this offseason.

Oct 23, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Dustin May (21) runs onto the field during player introductions before game one of the 2026 World Series against the Tampa Bay Rays at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images | IMAGN IMAGES via Reuters Connect

Under president of baseball operations Chaim Bloom, the St. Louis Cardinals took a savvy approach at the trade deadline, making a few smart trades.

There was a surprising amount of buzz about whether the Cardinals would act as buyers or sellers at the trade deadline this year, but with their early success this season, the team stuck to its rebuilding plan and sold. One of St. Louis' key deals involved trading starting pitcher Dustin May and reliever JoJo Romero to the Milwaukee Brewers in exchange for Alexander Frías and Josiah Ragsdale.

May spent the first five and a half seasons of his career with the Los Angeles Dodgers before being traded to the Boston Red Sox in 2025. After struggling in Boston, May signed a one-year, $12.5 million contract with the Cardinals, which also included a mutual option worth $20 million for 2027.

It's unlikely the Brewers will pick up the mutual option, so May will likely be on the open market again this offseason. The Cardinals' starting rotation was solid this season, but they could use a durable veteran to support their young rotation, especially one the team could sign to a short-term contract. Though a reunion with May makes sense on paper, St. Louis should avoid the 29-year-old and pursue free-agent pitchers.

May seems like a prime reunion candidate

Oct 15, 2026; Los Angeles, California, USA; Milwaukee Brewers pitcher Dustin May (21) throws during the second inning against the Los Angeles Dodgers in game four of the NLCS for the 2026 MLB Playoffs at Uniqlo Field at Dodger Stadium. Mandatory Credit: Kirby Lee-Imagn Images | IMAGN IMAGES via Reuters Connect

"Up for another go-around? May improved his value with what he did for the Cardinals, as evidenced by how much they got for him in their trade," MLB.com's Will Leitch wrote on Thursday. "But he struggled after moving to Milwaukee -- pending the World Series -- and it’s clear he’s not the No. 3 postseason starter the Brewers were hoping for. May still has a lively fastball and is relatively young compared to the market, as he won’t turn 30 until next September. You could argue that he still has a bit more to prove, and perhaps a return to St. Louis could help both parties once again."

St. Louis received a good return in the trade for May, but the 29-year-old hasn't lived up to expectations in Milwaukee. The Brewers haven't been able to rely on him as their No. 3 starting pitcher throughout the postseason. He's been inconsistent and has a 6.43 ERA through three playoff appearances this year.

Yes, the Cardinals could use a veteran pitcher with upside to bolster their rotation. With St. Louis in the middle of a rebuild, it would be great if the team could pull off a move similar to what they did with May this year and sign a starter with upside they could sell high at the trade deadline.

Unfortunately, it's hard to imagine teams would give up as much as the Brewers did to acquire May from the Cardinals next year, given his lack of production since the trade. If the Cardinals want to pursue free-agent starters with upside, they should look at players like Shane Bieber, Kris Bubic and Foster Griffin.